Реакция #66607

Уравнение реакции

2-isopropyl-4,5-dimethoxy-benzaldehyde

4-chloro-5-iodo-2-methylsulfanyl-pyrimidine

isopropyl magnesium bromide

→

(4-chloro-2-methylsulfanyl-pyrimidin-5-yl)-(2-isopropyl-4,5-dimethoxy-phenyl)-methanol

Выход 82.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   ДругоеThe mixture was quenched by the addition of brine
2. 2
   Экстракцияextracted with CH2Cl2
3. 3
   СушкаThe combined organic layers were dried over Na2SO4
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеPurification via flash chromatography (ethyl acetate)

Методика

To a solution of 4-chloro-5-iodo-2-methylsulfanyl-pyrimidine (1.10 g, 3.9 mmol) in 20 mL THF at −40° C. was added isopropyl magnesium bromide (2.3 mL, 2 M in THF)) over 5 minutes. After 30 minutes, 2-isopropyl-4,5-dimethoxy-benzaldehyde from step 3 (1.04 g, 4.6 mmol) was added and the solution was warmed to room temperature. The mixture was quenched by the addition of brine, and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (ethyl acetate) afforded (4-chloro-2-methylsulfanyl-pyrimidin-5-yl)-(2-isopropyl-4,5-dimethoxy-phenyl)-methanol (1.168 g, 82%) as a light yellow solid.

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